| Identification | Back Directory | [Name]
tromantadine | [CAS]
53783-83-8 | [Synonyms]
N-(1-Adamantyl)-2-[2-(dimethylamino)ethoxy]acetamide
Acetamide, 2-[2-(dimethylamino)ethoxy]-N-tricyclo[3.3.1.13,7]dec-1-yl- | [EINECS(EC#)]
258-770-0 | [Molecular Formula]
C16H28N2O2 | [MDL Number]
MFCD00869480 | [MOL File]
53783-83-8.mol | [Molecular Weight]
280.41 |
| Questions And Answer | Back Directory | [Description]
Tromantadine is an antiviral medicine used to treat herpes simplex virus. It is available in a topical gel under trade names Viru-Merz and Viru-Merz Serol. Its performance is similar to aciclovir. | [Mechanism of action]
Tromantadine inhibits the early and late events in the virus replication cycle.It changes the glycoproteins of the host cells, therefore impeding the absorption of the virus. It inhibits penetration of the virus. It also prevents uncoating of the virions.
|
| Chemical Properties | Back Directory | [Boiling point ]
434.5±28.0 °C(Predicted) | [density ]
1.09±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Oil | [pka]
14.58±0.20(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Originator]
Viru-Merz,Merz,W. Germany,1973 | [Uses]
Tromantadine hydrochloride is used as antiviral agent effective against herpes simplex infections. | [Definition]
ChEBI: Tromantadine is a secondary carboxamide. | [Manufacturing Process]
Adamantane is first reacted with chloroacetyl chloride to give
chloroacetylaminoadamantane.
2.3 g Na (0.1 g-atom) were dissolved in 75 ml dimethylamino-ethanol. Then
the excess alcohol was distilled off completely and the sodium salt developed
was dried in a vacuum. After drying, the salt was dissolved in about 200 ml
xylene. To thissolution.22.8 g (0.1 mol) chloroacetylaminoadamantane were added, heated for 10 hours under reflux in a 250-ml round-bottomed flask
with a reflux cooler, and the sodium chloride developed subsequently filtered
off.
Next the xylene was distilled away, the liquid residue dissolved in about 80 ml
carbon tetrachloride and the hydrochloride precipitated through introduction of
hydrochloric acid gas. The hydrochloride was dissolved in about 100 ml
acetone and the solvent subsequently distilled away, whereby excess
hydrochloric acid passed over with it. This operation was repeated until no
excess acid was present.
A large excess of petroleum ether was added in a 500 ml three-necked flask
provided with a stirrer and reflux cooler, to a concentrated acetonic solution of
the hydrochloride and stirred for at least 1 hour, whereby the desired
substance was deposited in a crystalline form. Finally, the substance was
filtered away and dried in a desiccator. 14 g of the substance (15% of theory)
were obtained. | [Therapeutic Function]
Antiviral |
|
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